Sherwood Homes with Pool

Welcome to Sherwood, Maryland—a hidden gem nestled in the heart of Talbot County. Known for its picturesque landscapes and serene atmosphere, Sherwood offers a unique blend of small-town charm and modern conveniences. With its lush greenery and proximity to the stunning Chesapeake Bay, residents enjoy a tranquil lifestyle that’s just a stone’s throw away from vibrant local attractions.

One of the standout features of homes in Sherwood is the availability of properties with pools. Imagine stepping out into your backyard oasis on a warm summer day, where a sparkling pool awaits. Whether you’re looking to host lively barbecues with friends, unwind after a long day, or simply soak up the sun, having a pool at your home enhances the joy of living in this beautiful area.

Sherwood is not just about beautiful homes; it’s also about community. Residents often gather at local parks, partake in seasonal events, and enjoy the picturesque walking trails that weave through the area. The welcoming atmosphere makes it easy to forge lasting friendships and create cherished memories.

With its prime location, Sherwood offers easy access to nearby towns, shopping, and dining options, while still providing a peaceful retreat from the hustle and bustle of city life. If you’re searching for a home with a pool in a charming community, Sherwood, MD, is the perfect destination to call home. Embrace the lifestyle you’ve always dreamed of in this idyllic setting!

Newest Sherwood Homes with Pool

$1,099,000

3 Beds ⋅ 3 Baths

Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

6670 Tilghman Island Rd, Sherwood

Listing courtesy of TTR Sotheby's International Realty. Contact:

$3,700,000

5 Beds ⋅ 7 Baths

GENEROUS PRICE REDUCTION!!!! This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play area. Large garage/barn to store all the water toys and pool equipment. It's currently being used as a Vacation Rental. Showings will be staggered between use.

21721 Heavenly Haven Rd, Sherwood

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

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